Sissy Maid to Be... Ch. 01

Prolog

I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Lizzy was unsure when I told her during the dating period of our relationship but figured it would be something we could work through together. I was happy dressing as a girl and of course looking slutty but then I found sissy maids on the internet. A whole new world opened up and I saw it as an outlet for my high stress career. The ability to be able to submit to another person and let all of the care of the world fall away was a dream that was unrealized by me in the past. It took some time to bring the subject up to my wife as I was extremely nervous at how she would react, but she was more than willing to try. Things evolved and it eventually ended up me serving as her sissy maid at home at times when the kids were over parents or friends house and serving as her personal sissy maid for fetish event. Things kept evolving past a point that this sissy thought they would ever go...

Chapter 1

It was the typical Friday when we woke up. Time to get the kids ready for school then practice where Lizzy's parents would come pick them up and keep them over for a night at the lake. Then to focus on work for both of us. We are lucky enough to have professional jobs that allow for us to work out of the house and we both took full advantage of working from home on a Friday. This Friday was a little different. It was the second Friday of the month and on that Friday Lizzy gets her special sissy maid for the evening. I look forward to this Friday as it is a chance for me to fully submit and have the illusion of giving up control although I could be classified as a power bottom. Lizzy especially looks forward to this event as it means a few days of loving attention from her husband after the dress up and serving is done. Lizzy is a 5'4" knockout. Her body is kept trim and tight by continuous workout sessions; her favorite being the kettlebell workout. Her blond hair goes just below the shoulders and accentuates her perfect face and plump lips. She loves taking her sissy maid to the fetish events because it gives her an opportunity to wear her corset with her micro mini-skirts and have all eyes on her in a personality she reserves only for these events. She is typically reserved in nature and has a hard time taking a lead role as a dominant. Through dress up and role playing she has evolved to a more dominant position but still backs down when I tell her it is far enough or if it is something I prefer not to do. A part of me would love to give up this control, but another part still requires the alpha male side to come out even if I am prancing around in petticoats and lace.

Kids were off to school and we were settled in to start our work day when Lizzy walked in and said "why don't you get ready this afternoon in your event sissy maid uniform, I have something special planned for tonight and I want it to be a surprise."

My event sissy maid uniform was an over the top pink sissy maid uniform. It is a custom order from birchplace. The dress is baby pink and zips up into a choker where a lock can be affixed at the back to make sure the dress doesn't come off. The pink is accentuated with white lace all around the sleeves and hems. The dress has a white lace pinafore that locks in the back all of this is accentuated with layers of petticoats that cause the skirt to stand out almost like a ballerina tutu. My special panties that were ordered are pink with layers of white ruffled lace which are visible when the petticoat is on. The outfit is topped off with white stay up nylons where the lace top is clearly visible and a pair of pink and white six inch locking heels with a pink bow at the toes. This outfit is typically reserved for going out to special events and I have won more than one sissy maid competition in this outfit.

My curiosity was peaked and so was what I had in my pants so I replied, "I don't recall any events going on this weekend, what were you thinking tonight?"

She replied, "Just get cleaned up and let me have this surprise tonight."

"So I am just supposed to get dressed up and not know what is happening next? I said.

"Yes, this is what you are always asking for, so please just do it tonight. It took a lot of planning and nerve for me to set this up without your involvement and I don't want to ruin it by giving you a chance to back out. I promise you will get the humiliation you have been asking for," she said.

So I agreed. Public humiliation is my biggest kink and I get plenty of it when out dressed like the sissy maid. Shopping at the grocery store in my maid uniform is already a head turner but when you add my 6-foot 2-inch 190 pound frame with an added 6-inch heels. There is no hiding that I am a sissy maid. I have been crossdressing for years and have perfected the art of makeup and styling my shoulder length brunette hair in a feminine manner, whether it be curling it with some cute bows to hold it out of my face or into a high ponytail with my sports bra and short shorts for my workouts.

I was unable to focus on work all that day wondering what would be the outing for the day and asked Lizzy multiple times what the plan was just to be met with "no, if you ask one more time I am not going to do it and I promise you this will be a night that you will never forget." So I sat at my desk with a hard on the entire afternoon until 3PM.

I jumped into the shower to clean up for tonight's plans. I wasn't sure what was going on but wanted to make sure I was prepared for anything. I typically stay shaved all over my body with the exception of the hair on my head year round. I wet my hair and used the feminine "color protection" shampoo and conditioner that Lizzy typically uses as it makes my hair smell perfumed with lilacs. I continued to shave my legs and arms so that I would have that smooth leg feeling when sliding my nylons up and not look like a hairy sissy who pays no attention to the feminine details that are important when going out as the sissy maid.

Freshly clean and shaven I stepped out of the shower and tied a towel around my head to help get into that feminine mood. Lizzy walked in and said, "Look at you all excited for your big evening, your little clitty looks like it is excited as well. We will have to get that taken care of so that we can get it locked up in your chastity device." Lizzy loved putting me in the mood by calling my cock a clitty. My cock is 7-inches hard and has some girth but when soft it can shrink to about 3-inches. She purposely ordered the smaller chastity to make it look more like a "sissy clitty" and put me in the right mindset when I was locked up and dressed up. She ordered me to the bed where she had handcuffs attached to the headboard and the baseboard and told me to lay on my stomach. She cuffed my hands to the headboard and my ankles to the baseboard in a spread eagle fashion, only being on my stomach. Once she was confident that I was secure, she pulled my hard clitty that was trapped under my stomach back between my legs. My cock was rock hard and ready to cum. She playfully gave me a few hard slaps on my exposed ass. Lizzy said, "Is my sissy girl all revved up for her evening of fun?"

I replied, "Yes mistress, your sissy is very excited, would mistress be willing to let her sissy know what the plan is for this evening?"

Lizzy replied, "Uh, uh, uh, that is a naughty sissy girl, asking when mistress already told you not to. I am going to make sure you understand your role tonight sissy and learn not to question my orders." At the end of this statement she produced her riding crop with the heart shaped leather end with the brass rivets. I didn't think it possible buy my cock grew even harder seeing this as I love a warm red ass, but that was not what I was going to get this time. Lizzy said, "On all fours sissy girl" but with the way I was tied to the bed it was impossible from me to raise my body more than 6 inches off of the bed. Lizzy grabbed my balls with one hand pulling them so that her hand was near the base of my cock and my balls were in a tight group on the other end outside of her hands and gave them a hard smack with the crop.

"Ow that hurt," I cried.

"Ow that hurt, who? Sissy", she replied.

"Come on Lizzy, you know I like..."

Smack! That one hurt and took my breath away and my eyes welled up in tears.

"You will address me as mistress, do you got that," Lizzy said.

"Yes, mistress," I meekly replied.

"Good girl, now to take care of that nasty little thing between your legs, so you can finish getting ready." At this she placed a pink blindfold over my eyes and walked out of the room. I was still rock hard even though my balls were aching from the hard smack I had received from my insolence. I heard her walk back into the room and heard a slight rattling but couldn't quiet place just what the sound meant.

Lizzy grabbed my hard cock that was back between my legs and said, "Why are you laying back down? I told you to be on all fours."

"Sorry Mistress," I replied and pushed myself up as much as possible and was elevated with my stomach about 6-inches off of the bed.

Lizzy grabbed my hard cock and said, "Look at how excited your little clitty is, we will never be able to get it locked up like this." At this she gave my cock a tug like she was milking a cow and I felt her fingers brush the tip of my cock. Not being able to see with the blindfold on I was surprised to feel her fingertips enter my mouth with a salty thick taste on them. "Your dripping your milk all over sissy we need to get this taken care of so your pretty dress doesn't get stained tonight, don't we sissy? Would you like mistress to milk you dry so your panties don't get all wet?"

"Yes, mistress. I would love to cum so I don't make a mess of my dress," I replied. "Will you please milk your sissy, mistress?"

Lizzy continued to gently pull on my hard cock and used the tip of her manicured fingernail to trace little circles on my exposed ass. Getting me close but stopping before I could feel release.

"You and I both know that if I let you cum, you will get back to your macho frame of mind and not want to put on your pretty sissy maid dress and wait on me tonight," Lizzy said.

"I promise I still will mistress. Please let me cum and I will do anything you want." I replied.

"Ha, how many times have I heard that only to let you cum and you back out of your promises? You and I both know that you need to be full of your sissy milk to be obedient and give me the attention that I deserve," Lizzy said.

"Well you and I both know, mistress, that in my current state there is no way that I will fit into that chastity device." I teased. I knew she was exactly right about letting me cum and my backing out. How many times had I promised to do something humiliating of my own making only to back out once my cock felt release?

Lizzy said, "Well I can always smack your balls some more with the riding crop, that might take care of our little problem." The thought of having my balls smacked again caused me to drop to my stomach in fear. "But I think I have a better idea that I have been wanting to try. Get back on all fours sissy."

The threat of the riding crop on my balls gone I willfully rose as much as possible off of the bed then I heard the familiar rattle that I couldn't quite place. I tried to peak though my blindfold but was unable to see anything. Then I heard the rattling come closer and Lizzy said, "well you are right about not being able to fit into the chastity and I really don't want to cause you more pain right now, so let's try this" At that Lizzy slid a mixing bowl under me and I instantly knew the sound. It was water with ice. She pushed my midsection down laughing and said, "This should shrink that hard cock back to a sissy's clitty."

I was in shock feeling my hard cock submerged in ice water and instantly tried to rise back up. Lizzy pushed me back down submerging my cock in the ice water again.

"Now, now sissy. We need to make sure you get your little clitty back in its true form. We can't have your panties in a tent for our fun tonight, now can we?" She climbed up on the bed and sat on my bare bottom forcing me to stay fully emerged in the freezing ice water. Still unable to see but somewhat able to sense what was going on, Lizzy dialed her cell phone.

"Oh hi, Tiffany...yeah I forgot we had plans tonight...sorry to cancel last minute but I forgot it was Jeremy's night to turn into a girl...yeah he is going to be in his maid uniform tonight...oh I have some big plans for her tonight, she is always begging for me to take total control and surprise her and I plan on it tonight...haha, of course you can come over if you like, she is always begging me to let her serve as the sissy maid, you should bring Steve along as well. I am sure I can get sissy jenny to suck his cock if you want...haha, yeah she will do anything I tell her when she is in the right mindset...yeah I know it is far, you will have to meet her another time...well I should let you go I am in the middle of turning him into a girl right now...take care...bye bye" With that she hung up the phone. Tiffany was one the few friends that Lizzy had told about my crossdressing and fetishes. I encouraged her to let her know so she would have someone to talk to about how she was feeling about my dressing up. I was turned on at the thought of Tiffany finally seeing me dressed up and submitting to a superior woman. The thought of what comments she would have always got me turned on, but it was impossible to get hard with my cock and balls submerged in ice water with Lizzy sitting on my ass so that I couldn't pull them out.

Lizzy said, "I am going to get off of you but you better not lift out of that water, do you understand?"

I replied, "Yes mistress." And with that she got off of me. My cock was still submerged but by now I had lost all feeling in it.

Lizzy bent down to look at my frozen member and rose up. "That should about do it. Lift up out of the water sissy." Gratefully I lifted out of the water and heard her laugh. "I think I overdid it sissy. I didn't think it could ever get that small but I was wrong. I think you will easily slip out of a normal chastity device. Good thing I ordered the extra small."

Normally I would get hard again at a comment like this but with my cock and balls still frozen there was no feeling. She un-cuffed my left arm and my left foot and told me to roll onto my back. Once on my back she refastened the cuffs. She left the blindfold on me so that I couldn't see. I felt her hovering over me then heard the click of her camera phone. "I can't believe how small it is. I have to send this to Tiffany so she can see why you love wearing pretty dresses" I heard the swoosh of the text being sent then Lizzy laughing. "Tiffany said she can't hardly see it. That it is smaller than a baby's." My cock twitched at this comment and Lizzy said, "Uh oh, we better get that little clitty locked up while we can." I felt her slide the ring over my balls and pull my cock through. I felt her rub lotion on my cock then felt the tube slide on. Then came the click of the key turning in the chastity tube and there was no getting out until mistress decided I had earned it.

She moved off the bed and removed my blindfold. "Do you promise to do whatever I tell you tonight?" Lizzy asked.

"Of course, mistress." I replied.

"I mean anything and everything I say? I spent a lot of time arranging this and I know it is what you really want, even though you may try to back out," she said.

At this I paused for a minute and she said, "See you are already hesitating and you don't even know what it is, I promise this will be a night you will never forget."

I replied, "yes mistress" not fully knowing what the night that lay ahead had in store but already dripping with precum thinking of the possibilities.

To be continued...